DOCSLIB.ORG

(12) United States Patent (10) Patent No.: US 7,776,844 B2 Yu Et Al

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
(12) United States Patent (10) Patent No.: US 7,776,844 B2 Yu Et Al USOO777684.4B2 (12) United States Patent (10) Patent No.: US 7,776,844 B2 Yu et al. (45) Date of Patent: Aug. 17, 2010 (54) N-(PHOSPHONOALKYL)-AMINO ACIDS, 7,429,575 B2 9/2008 Yu et al. DERVATIVES THEREOF AND 2005, 016491.6 A1 7/2005 Leadbetter et al. COMPOSITIONS AND METHODS OF USE OTHER PUBLICATIONS (76) Inventors: Ruey J. Yu, 655 Stump Rd., Chalfont, Struninet al., 1989, CAS. 111:233525.* PA (US)18914; Eugene J. Van Scott, 3 Shi et al., 2004, CAS;142. 231739.* Hidden La., Abington, PA (US) 19001 Li et al., 2005, CAS; 143: 158351.* Sandeman et al., 2002, CAS: 137:274431.* (*) Notice: Subject to any disclaimer, the term of this Single co's i. 164: patent is extended or adjusted under 35 Stahl e et et al., al., 1995, CAS:si. 124:563.10.* U.S.C. 154(b) by 0 days. Jezowska-Bojczuk et al., 1994, CAS: 120:28.1638.* Strumin et al., 1989, CAS: 111:194894.* (21) Appl. No.: 12/428,906 Balthazor et al., 1987, CAS: 106:50457.* The Merck Index. "An Encyclopedia of Chemicals, Drugs, and (22) Filed: Apr. 23, 2009 Biologicals.” (2001) p. 1768, (2 pgs.), 13th Edition, O'Neil et al. (Ed.), Merck & Co., Inc., Whitehouse Station, N.J. (65) Prior Publication Data Wester et al., 1991, CAS: 114:242443. US 2009/0208499 A1 Aug. 20, 2009 * cited by examiner Related U.S. Application Data Primary Examiner Rei-tsang Shiao - - - (74) Attorney, Agent, or Firm Panitch Schwarze Belisario & (62) Division of application No. 12/194203, filed on Aug. Nadel LLP 19, 2008, now Pat. No. 7,572,776, which is a division of application No. 1 1/621,287, filed on Jan. 9, 2007, (57) ABSTRACT now Pat. No. 7,429,575. The present invention relates to an N-(phosphonoalkyl)- (60) Eyal application No. 60/757,614, filed on Jan. amino acid, a related compound or a derivative thereof, the s N-(phosphonoalkyl)-amino acid, related compound or derivative thereof being in a form as a free acid, salt, partial (51) Int. Cl. salt, lactone, amide or ester, or in Stereoisomeric or non 52 it.too (2006.01) S14/114: 514/399 Stereoisomeric form, other than N-(phosphonomethyl)-gly . Fi ld fici - - - - - ificati- - - - - -s - - - - - - - h- - - - - s 514/114 cine or N.N-bis(phosphonomethyl)-glycine. Also included is (58) Field of Classification Search ................. s a composition including an N-(phosphonoalkyl)-amino acid, 514399; 548/335.5, 170; 558/170. 156 a related compound or a derivative thereof in a form as a free See application file for complete search history. acid, salt, partial salt, lactone, amide or ester, or in Stereoiso (56) References Cited meric or non-stereoisomeric form, and a cosmetically or pharmaceutically acceptable vehicle for topical or systemic U.S. PATENT DOCUMENTS administration to a mammalian Subject, as well as a method of 3.288,846 A 11, 1966 Irani et al. administering an effective amount of Such a composition for 3,799,758 A 3, 1974 Franz alleviating or improving a condition, disorder, symptom or 3,853,530 A 12, 1974 Franz syndrome associated with at least one of a nervous, vascular, 5,259,974 A 11/1993 Chen et al. musculoskeletal or cutaneous system. 5,414,112 A * 5/1995 Dragisich .................... 562/12 6,229,045 B1 5/2001 Ringer et al. 17 Claims, No Drawings US 7,776,844 B2 1. 2 N-(PHOSPHONOALKYL)-AMINO ACIDS, that Such compounds are useful for treating various medical DERVATIVES THEREOF AND and cosmetic conditions in animals, such as mammals, and COMPOSITIONS AND METHODS OF USE including humans. CROSS-REFERENCE TO RELATED BRIEF SUMMARY OF THE INVENTION APPLICATIONS One aspect of the present invention relates to an N-(phosphonoalkyl)-amino acid, a related compound or a This application is a divisional application of U.S. patent derivative thereof, the N-(phosphonoalkyl)-amino acid, application Ser. No. 12/194.203, filed Aug. 19, 2008, now 10 related compound or derivative thereof being in a form as a allowed, which is a divisional application of U.S. patent free acid, salt, partial salt, lactone, amide or ester, or in Ste application Ser. No. 1 1/621,287, filed Jan. 9, 2007, now U.S. reoisomeric or non-stereoisomeric form, other than Pat. No. 7,429,575, issued Sep. 30, 2008, which claims the N-(phosphonomethyl)-glycine or N.N-bis(phosphonom benefit under 35 U.S.C.S 119(e) of U.S. Provisional Applica ethyl)-glycine. 15 Another aspect of the present invention relates to an tion No. 60/757,614, filed Jan. 10, 2006. The entire disclo N-(phosphonoalkyl)-amino acid compound, a related com sures of all of the above applications are hereby incorporated pound or a compound derived therefrom, the compound herein by reference. includes the group consisting of N-(phosphonoalkyl)-proline and a compound or derivative thereof having the following BACKGROUND OF THE INVENTION formula: The present invention relates to an N-(phosphonoalkyl)- amino acid, a related compound or a derivative thereof, the wherein R is H. an alkyl group having 1 to 19 carbon atoms, N-(phosphonoalkyl)-amino acid, related compound or an aryl group having 6 to 19 carbonatoms oran aralkyl group derivative thereof being in a form as a free acid, salt, partial 25 having 7 to 19 carbon atoms; and R can also carry —OH, salt, lactone, amide or ester, or in Stereoisomeric or non SH, -SCH, -NH = NR,R, COR - NHCONH2, Stereoisomeric form, other than N-(phosphonomethyl)-gly —NHC(=NR)NH, imidazole, pyrrolidine or other hetero cine or N,N-bis(phosphonomethyl)-glycine. The present cyclic group; m is an integer from 0 to 5; R is a phospho noalkyl group having a formula (HO)2PO(CH), ; R is H invention also relates to a composition including an 30 or a phosphonoalkyl group having a formula (HO)PO N-(phosphonoalkyl)-amino acid, a related compound or a (CH), ; n is an integer from 1 to 9; R is —NH2 or —ORs. derivative thereof in a form as a free acid, salt, partial salt, Rs is H, an alkyl group having 1 to 19 carbon atoms, an aryl lactone, amide or ester, or in Stereoisomeric or non-stereoi group having 6 to 19 carbonatoms or an aralkyl group having Someric form, and a cosmetically orpharmaceutically accept 7 to 19 carbon atoms; and the Hattached to any carbon atom able vehicle for topical or systemic administration to a mam 35 can be substituted by I, F, Cl, Br, OH or an alkoxy group malian Subject, as well as a method of administering an having 1 to 9 carbon atoms; and wherein the N-(phospho effective amount of Such a composition for alleviating or noalkyl)-amino acid, related compound or derivative thereof improving a condition, disorder, symptom or syndrome asso is in a form as a free acid, salt, partial salt, lactone, amide or ester, or in a stereoisomeric or non-stereoisomeric form; pro ciated with at least one of a nervous, vascular, musculoskel 40 vided that the compound is not N-(phosphonomethyl)-gly etal or cutaneous system. cine or N,N-bis(phosphonomethyl)-glycine. N-(Phosphonomethyl)-glycine is listed as glyphosate, Another aspect of the present invention relates to a com C.H.N.O.P. molecular weight 169, in The Merck Index, 13" position comprising an N-(phosphonoalkyl)-amino acid, a edition, 2001, page 803. The mono (isopropylamine) salt of 45 related compound or a derivative thereof, the N-(phospho N-(phosphonomethyl)-glycine is a primary active ingredient noalkyl)-amino acid, related compound or derivative thereof in Roundup(R) herbicide. N,N-Bis(phosphonomethyl)-gly being in a form as a free acid, salt, partial salt, lactone, amide cine is listed as glyphosine, CHNOP, molecular weight or ester, or in Stereoisomeric or non-stereoisomeric form, and 263, in The Merck Index, 13' edition, 2001, page 804. This a cosmetically or pharmaceutically acceptable vehicle for compound is listed as plant growth regulator known to cause 50 topical or systemic administration to a mammalian Subject. chlorosis in green plants, and also used as a chemical ripener. Yet another aspect of the present invention relates to a U.S. Pat. No. 3.288,846 entitled “Processes for Preparing method of alleviating or improving a condition, disorder, Organo-Phosphonic Acids’ describes a synthesis of N-Sub symptom or syndrome associated with at least one of a ner stituted aminomethylenephosphonic acid. U.S. Pat. No. Vous, vascular, musculoskeletal or cutaneous system, the 3,799,758 entitled “N-Phosphonomethyl-Glycine Phytotoxi 55 method comprising administering to a mammalian Subject cant Compositions' describes N-(phosphonomethyl)-glycine having the disorder, symptom or syndrome an amount effec tive for alleviating or improving the condition, disorder, and its derivatives useful as phytotoxicants and herbicides. symptom or syndrome of a composition comprising an U.S. Pat. No. 3,853,530 entitled “Regulating Plants with N-(phosphonoalkyl)-amino acid, a related compound or a N-phosphonomethyl-Glycine and Derivatives Thereof 60 derivative thereof, the N-(phosphonoalkyl)-amino acid, describes the use of N-Phosphonomethyl-glycine and deriva related compound or derivative thereof being in a form as a tives useful for regulating the natural growth and develop free acid, salt, partial salt, lactone, amide or ester, or in Ste ment of plants. reoisomeric or non-stereoisomeric form, and a cosmetically There has been no teaching, Suggestion or implication or pharmaceutically acceptable vehicle for topical or sys about the use of N-(phosphonomethyl)-glycine or its deriva 65 temic administration to the mammalian Subject. tives for topical or systemic administration to mammals, The cosmetic conditions and medical disorders, symptoms including humans.
Load more

Recommended publications
  • Generate Metabolic Map Poster
    Authors: Pallavi Subhraveti Ron Caspi Peter Midford Peter D Karp An online version of this diagram is available at BioCyc.org. Biosynthetic pathways are positioned in the left of the cytoplasm, degradative pathways on the right, and reactions not assigned to any pathway are in the far right of the cytoplasm. Transporters and membrane proteins are shown on the membrane. Ingrid Keseler Periplasmic (where appropriate) and extracellular reactions and proteins may also be shown. Pathways are colored according to their cellular function. Gcf_003855395Cyc: Shewanella livingstonensis LMG 19866 Cellular Overview Connections between pathways are omitted for legibility.
    [Show full text]
  • Antiviral Compounds Antivirale Verbindungen Composes Antiviraux
    (19) TZZ_Z _T (11) EP 1 778 702 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07F 9/141 (2006.01) C07D 207/08 (2006.01) 13.07.2011 Bulletin 2011/28 A61K 31/662 (2006.01) A61P 31/12 (2006.01) (21) Application number: 05791144.8 (86) International application number: PCT/US2005/025503 (22) Date of filing: 18.07.2005 (87) International publication number: WO 2006/020276 (23.02.2006 Gazette 2006/08) (54) ANTIVIRAL COMPOUNDS ANTIVIRALE VERBINDUNGEN COMPOSES ANTIVIRAUX (84) Designated Contracting States: (74) Representative: Reitstötter - Kinzebach AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Patentanwälte HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI Sternwartstrasse 4 SK TR 81679 München (DE) Designated Extension States: AL BA HR MK YU (56) References cited: EP-A- 1 337 550 WO-A-00/09543 (30) Priority: 16.07.2004 US 588633 P WO-A-00/59929 WO-A-98/17679 27.07.2004 US 591635 P WO-A-99/07733 WO-A-02/060926 WO-A-03/053349 WO-A-03/064416 (43) Date of publication of application: WO-A-03/064455 WO-A-03/064456 02.05.2007 Bulletin 2007/18 WO-A-03/066103 WO-A-03/099274 WO-A-03/099316 US-A1- 2003 186 895 (60) Divisional application: US-A1- 2003 224 977 US-A1- 2004 048 802 10178084.9 / 2 316 839 US-B1- 6 608 027 (73) Proprietor: GILEAD SCIENCES, INC.
    [Show full text]
  • Purification and Characterization of the Higher Plant Enzyme L-Canaline Reductase (L-Canavanine Catabolism/Plant Nitrogen Metabolism/Leguminosae) GERALD A
    Proc. Natd. Acad. Sci. USA Vol. 89, pp. 1780-1784, March 1992 Biochemistry Purification and characterization of the higher plant enzyme L-canaline reductase (L-canavanine catabolism/plant nitrogen metabolism/Leguminosae) GERALD A. ROSENTHAL T. H. Morgan School of Biological Sciences, University of Kentucky, Lexington, KY 40506 Communicated by John S. Boyer, December 3, 1991 (receivedfor review April 20, 1991) ABSTRACT A newly discovered enzyme, L-canaline re- oglutaric acid to generate stoichiometrically a canaline-2- ductase (NADPH:L-canaline oxidoreductase, EC 1.6.6.-), has oxoglutaric acid oxime (5). Canaline also reacts readily with been isolated and purified from 10-day-old leaves of the jack the pyridoxal phosphate moiety of vitamin B6-containing bean Canavalia ensiformis (Leguminosae). This higher plant is enzymes to form a stable, covalently linked complex (6, 7). representative of a large number of legumes that synthesize In vitro analysis of canaline interaction with homogeneous L-canavanine, an important nitrogen-storing nonprotein amino ornithine aminotransferase (ornithine-oxo-acid aminotrans- acid. Canavanine-storing legumes contain arginase, which ferase; L-ornithine:2-oxo-acid aminotransferase, EC hydrolyzes L-canavanine to form the toxic metabolite L-cana- 2.6.1.13) reveals its marked ability to form an oxime complex line. Canaline reductase, having a mass of =167 kDa and with and thereby inhibit this pyridoxal phosphate-dependent composed of 82-kDa dimers, catalyzes a NADPH-dependent enzyme (8). As little as 10 nM canaline causes a significant reductive cleavage of L-canaline to L-homoserine and ammo- reduction in ornithine aminotransferase activity (9). nia. This is the only enzyme known to use reduced NADP to Canavanine-storing legumes can accumulate high levels of cleave an O-N bond.
    [Show full text]
  • | Mo Naman Attituunika Mitatti
    |MO NAMAN ATTITUUNIKAUS009962450B2 MITATTI (12 ) United States Patent (10 ) Patent No. : US 9 , 962 , 450 B2 Kraynov et al. ( 45) Date of Patent : May 8 , 2018 ( 54 ) METHOD OF TREATING HEART FAILURE 4 ,659 ,839 A 4 / 1987 Nicolotti et al . WITH MODIFIED RELAXIN POLYPEPTIDES 4 ,670 ,417 A 6 / 1987 Iwasaki et al. 4 ,671 , 958 A 6 / 1987 Rodwell et al. 4 ,680 , 338 A 7 / 1987 Sundoro ( 71) Applicant : AMBRX , INC . , La Jolla , CA (US ) 4 ,689 ,406 A 8 / 1987 Banks et al . 4 ,699 ,784 A 10 / 1987 Shih et al . ( 72 ) Inventors : Vadim Kraynov , San Diego , CA (US ) ; 4 ,738 , 921 A 4 / 1988 Belagaje et al. Nick Knudsen , San Diego , CA (US ) ; 4 ,755 ,465 A 7 / 1988 Gray et al. 4 ,837 , 148 A 6 / 1989 Cregg Amha Hewet, Chula Vista , CA (US ) ; 4 ,859 ,600 A 8 / 1989 Gray et al . Kristine De Dios, San Diego , CA (US ) ; 4 , 876 , 197 A 10 / 1989 Burke et al. Jason Pinkstaff , Encinitas, CA (US ) ; 4 , 880 ,734 A 11/ 1989 Burke et al . Lorraine Sullivan , San Diego , CA 4 , 902 ,502 A 2 / 1990 Nitecki et al . 4 , 904 , 584 A 2 / 1990 Shaw ( US ) 4 ,929 , 555 A 5 / 1990 Cregg et al. 5 ,021 , 234 A 6 / 1991 Ehrenfeld (73 ) Assignee : AMBRX , INC. , La Jolla , CA (US ) 5 ,089 ,398 A 2 / 1992 Rosenberg et al . 5 , 122 ,614 A 6 / 1992 Zalipsky ( * ) Notice : Subject to any disclaimer , the term of this 5 , 145 , 962 A 9 / 1992 Hudson et al.
    [Show full text]
  • Zone Finhibton Inmillimeters
    US006191168B1 (12) United States Patent (10) Patent N0.: US 6,191,168 B1 Rubenstein (45) Date of Patent: Feb. 20, 2001 (54) METHODS FOR THE USE OF NONPROTEIN CA 126: 268319, Breton et al, 1997.* AMINO ACIDS AS THERAPEUTIC AGENTS Bell. (1958). “Canavanine and Related Compounds in Legu minosae,” Biochem J. 70:617—619. (75) Inventor: Edward Rubenstein, 5 Waverly Pl., Bisby et al. (1994). Phytochemical Dictionary of the Legu Hillsborough, CA (US) 94010 minose, vol. 1—2. (Title page and table of contents only). Butler et al. (1967). “Uptake and Metabolism of Inorganic (73) Assignee: Edward Rubenstein, Hillsborough, CA Forms of Selenium—75 by Spiroa'ela Oligorrhiza, ” Aust. J. (Us) Biol. Sci. 20:77—86. Conn. (1981). “Secondary Plant Products” The Biochemistry (*) Notice: Under 35 U.S.C. 154(b), the term of this of Plants vol. 7(Title page and table of contents only). patent shall be extended for 0 days. CoWie et al. (1957). “Biosynthesis by Escherichia Coli of Active Altered Proteins Containing Selenium Instead of (21) Appl. No.: 09/324,181 Sulfur,” Biochem et Biophysica Acta. 26:252—261. Gennaro ed. (1995). Remington." The Science and Practice Filed: Jun. 1, 1999 (22) The Science and of Pharmacy (Title page and table of Related US. Application Data contents only). (60) Provisional application No. 60/087,746, ?led on Jun. 2, (List continued on neXt page.) 1998. Primary Examiner—Rebecca Cook (51) Int. Cl.7 ................................................. .. A61K 31/195 (74) Attorney, Agent, or Firm—Morrison & Foerster LLP (52) US. Cl. ........................ .. 514/561; 514/210; 514/274; 514/419; 514/423; 514/315; 514/354; 514/538; (57) ABSTRACT 514/562; 514/563; 514/564; 514/565 Provided are compositions comprising nonprotein amino (58) Field of Search ..................................
    [Show full text]
  • Download Product Insert (PDF)
    PRODUCT INFORMATION L-Canaline Item No. 9002357 CAS Registry No.: 496-93-5 Formal Name: O-amino-L-homoserine O MF: C H N O 4 10 2 3 O FW: 134.1 HO NH2 Purity: ≥95% NH Stability: ≥2 years at -20°C 2 Supplied as: A crystalline solid Laboratory Procedures For long term storage, we suggest that L-canaline be stored as supplied at -20°C. It should be stable for at least two years. L-Canaline is supplied as a crystalline solid. A stock solution may be made by dissolving the L-canaline in the solvent of choice. L-Canaline is soluble in organic solvents such as DMSO which should be purged with an inert gas. The solubility of L-canaline in this solvent is approximately 1 mg/ml. Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of L-canaline can be prepared by directly dissolving the crystalline solid in aqueous buffers. The solubility of L-canaline in PBS, pH 7.2, is approximately 10 mg/ml. We do not recommend storing the aqueous solution for more than one day. Description L-Canaline is an aminooxy analog of ornithine that irreversibly inhibits aminotransferases (transaminases), 1-3 including ornithine aminotransferase (Ki = 2 µM). It forms oximes with α-keto acids and aldehydes, most notably with pyridoxal phosphate, an essential cofactor of aminotransferases.3 L-Canaline is naturally found in plants, including legumes, and is involved in the metabolism of L-canavanine, an aminooxy analog of arginine.4 It is cytotoxic to a range of organisms, including bacteria, insects, and parasites.2,4,5 References 1.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 9,452.222 B2 Kraynov Et Al
    USOO9452222B2 (12) United States Patent (10) Patent No.: US 9,452.222 B2 Kraynov et al. (45) Date of Patent: Sep. 27, 2016 (54) NUCLEIC ACIDS ENCODING MODIFIED 4,680,338 A 7, 1987 Sundoro RELAXN POLYPEPTIDES 4,689,406 A 8, 1987 Banks et al. 4,699,784. A 10, 1987 Shih et al. 4,738,921 A 4, 1988 Belagaje et al. (71) Applicant: Ambrx, Inc., La Jolla, CA (US) 4,755.465 A 7/1988 Gray et al. 4,837,148 A 6/1989 Cregg (72) Inventors: Vadim Kraynov, San Diego, CA (US); 4,859,600 A 8/1989 Gray et al. Nick Knudsen, San Diego, CA (US); 4,876, 197 A 10, 1989 Burke et al. 4,880,734 A 11/1989 Burke et al. Ahma Hewet, Chula Vista, CA (US); 4.902,502 A 2f1990 Nitecki et al. Kristine De Dios, San Diego, CA (US); 4,904,584 A 2, 1990 Shaw Jason Pinkstaff, Encinitas, CA (US); 4,929,555 A 5/1990 Cregg et al. Lorraine Sullivan, San Diego, CA 5,021,234 A 6, 1991 Ehrenfeld (US) 5,089,398 A 2/1992 Rosenberg et al. 5,122,614 A 6/1992 Zalipsky 5,145,962 A 9, 1992 Hudson et al. (73) Assignee: AMBRX, INC., La Jolla, CA (US) 5,162,601 A 11/1992 Slightom 5,219,564 A 6/1993 Zalipsky et al. (*) Notice: Subject to any disclaimer, the term of this 5,229,490 A 7, 1993 Tam patent is extended or adjusted under 35 5,231,178 A 7, 1993 Holtz et al.
    [Show full text]
  • United States Patent Office Patented Nov
    3,704,246 United States Patent Office Patented Nov. 28, 1972 2 (I) R 3,704,246 AMNO ACD DERVATIVES ( CH).--N Miklos Bodanszky, Shaker Heights, Ohio, assignor to R2-C YoH-R E. R. Squibb & Sons, Inc., New York, N.Y. No Drawing. Continuation-in-part of application Ser. No. R-i-o-c6 798,790, Feb. 12, 1969, which is a continuation-in-part wherein R is the residue of an a-amino acid, R1 is hydro of abandoned application Ser. No. 451,609, Apr. 28, gen, lower alkyl, hydroxy-substituted lower alkyl, or 1965. This application Dec. 16, 1970, Ser. No. 98,924 lower alkyl lower alkoxy; R and R3 each is hydrogen, int. C. C07d 87/54 lower alkyl, hydroxy-substituted lower alkyl, lower alkyl U.S. C. 260-333 9 Claims 10 lower alkoxy, or R and R3 together with the carbons to which they are joined form a phenyl ring which may be unsubstituted or substituted by halogen or nitro, and m ABSTRACT OF THE DESCLOSURE is an integer from 0 to 3. New lactone intermediates useful in the synthesis of 5 DETAILED DESCRIPTION OF THE INVENTION peptides are prepared by reacting an a-amino acid with Any a-amino acid may be treated according to this an active carbonyl compound which forms a Schiff's base. invention. This includes the naturally occurring ox-amino The latter is treated with a condensing agent so that acids see for example, Hackh's Chemical Dictionary, cyclization occurs and a lactone is formed from which a 3rd ed.
    [Show full text]
  • (12) Patent Application Publication (10) Pub. No.: US 2007/0161543 A1 Yu Et Al
    US 2007 O161543A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0161543 A1 Yu et al. (43) Pub. Date: Jul. 12, 2007 (54) N-(PHOSPHONOALKYL)-AMINO ACIDS, (52) U.S. Cl. .............................. 514/7: 514/114: 530/331; DERVATIVES THEREOF AND 558/170 COMPOSITIONS AND METHODS OF USE (76) Inventors: Ruey J. Yu, Chalfont, PA (US); Eugene J. Van Scott, Abington, PA (US) (57) ABSTRACT Correspondence Address: AKN GUMPSTRAUSS HAUER & FELD The present invention relates to an N-(phosphonoalkyl)- 6. COMMERCE SQUARE amino acid, a related compound or a derivative thereof, the 2005 MARKET STREET, SUITE 2200 N-(phosphonoalkyl)-amino acid, related compound or PHILADELPHIA, PA 19103 (US) derivative thereof being in a form as a free acid, salt, partial salt, lactone, amide or ester, or in Stereoisomeric or non (21) Appl. No.: 11/621,287 Stereoisomeric form, other than N-(phosphonomethyl)-gly (22) Filed: Jan. 9, 2007 cine or N.N-bis(phosphonomethyl)-glycine. Also included is a composition including an N-(phosphonoalkyl)-amino acid, Related U.S. Application Data a related compound or a derivative thereof in a form as a free (60) Provisional application No. 60/757,614, filed on Jan. acid, salt, partial salt, lactone, amide or ester, or in Stereoi 10, 2006. sy u. Is Someric or non-stereoisomeric form, and a cosmetically or pharmaceutically acceptable vehicle for topical or systemic Publication Classification administration to a mammalian Subject, as well as a method of administering an effective amount of Such a composition (51) Int. Cl. A6 IK 38/05 (2006.01) for alleviating or improving a condition, disorder, symptom A6 IK 3/66 (2006.01) or syndrome associated with at least one of a nervous, C07K 5/10 (2006.01) vascular, musculoskeletal or cutaneous system.
    [Show full text]
  • Generated by SRI International Pathway Tools Version 25.0, Authors S
    Authors: Pallavi Subhraveti Ingrid Keseler Quang Ong Ron Caspi An online version of this diagram is available at BioCyc.org. Biosynthetic pathways are positioned in the left of the cytoplasm, degradative pathways on the right, and reactions not assigned to any pathway are in the far right of the cytoplasm. Transporters and membrane proteins are shown on the membrane. Tim Holland Peter D Karp Periplasmic (where appropriate) and extracellular reactions and proteins may also be shown. Pathways are colored according to their cellular function. Saur904776Cyc: Staphylococcus aureus aureus IS-24 Cellular Overview Connections between pathways are omitted for legibility. Anamika Kothari guaninehypoxanthine indole- pro 3-acetate (S)-lactate (S)-lactate uracil H + H + H + H + H + H + H + H + H + ammonium IS24_0964 IS24_2784 AtpC AtpF AtpI AtpA AtpD AtpE AtpB AtpH AtpG Amt PbuG PutP PyrP IS24_1600 + + + + + + + + + indole- H H H H H H H H H uracil (S)-lactate (S)-lactate ammonium 3-acetate guanine pro hypoxanthine Cofactor, Prosthetic Group, Electron Carrier, and Vitamin Biosynthesis Chemoautotrophic Amino Acid Degradation Energy Metabolism Detoxification UDP-N-acetyl- an [apo BCAA an apo-[methylmalonyl- campest- a (3R)-3- 3-(4- valine degradation I a [formate C testosterone a phosphate cob(II)yrinate a,c- glutamine SAM a reduced flavodoxin α-D-muramoyl- di-trans,octa-cis 4-methyl-2- dehydrogenase CoA:pyruvate biotin 5-hydroxytryptophol β hydroxyhexanoyl- hydroxyphenyl) flavin biosynthesis I (bacteria and plants) L-ascorbate biosynthesis V L-ascorbate
    [Show full text]
  • Pka Data Compiled by R
    pKa Data Compiled by R. Williams page-1 pKa Values INDEX Inorganic 2 Phenazine 24 Phosphates 3 Pyridine 25 Carboxylic acids 4, 8 Pyrazine 26 Aliphatic 4, 8 Aromatic 7, 8 Quinoline 27 Phenols 9 Quinazoline 27 Alcohols and oxygen acids 10, 11 Quinoxaline 27 Amino Acids 12 Special Nitrogen Compounds 28 Peptides 13 Hydroxylamines 28 Nitrogen Compounds 14 Hydrazines 28 Aliphatic amines 15, 17, 19 Semicarbazones 28 Cyanoamines 16 Amidoximes 28 Anilines 17, 18, 20 Thiols 29 Nucleosides 21 Carbon Acids 30,31 Special Table Heterocycles 22 Indicators 31 Acridine 23 References 32-34 Benzoquinoline 24 Cinnoline 23 Hydantoin 24 Imidazole 24 For complex chelating agents, see also reference 77. Note. This document was compiled by W.P. Jencks and has been added to by F.H. Westheimer pKa Data Compiled by R. Williams page-2 ACIDS Compound pK Ref. H3PO2 2.0, 2.23* 28 H2PO4– 7.21* 77 AgOH 3.96 4 HPO4_ 12.32* 77 Al(OH)3 11.2 28 H3PO3 2.0 28 As(OH)3 9.22 28 H PO – 6.58* 77 H3AsO4 2.22, 7.0, 13.0 28 2 3 H4P2O7 1.52* 77 H2AsO4– 6.98* 77 H P O – 2.36* 77 HAsO4* 11.53* 77 3 2 7 = As2O3 0 4 H2P2O7 6.60* 77 H3AsO3 9.22* HP2O7= 9.25* 77 H3BO3 9.23* 28 HReO4 -1.25 30 H2B4O7 4.00 34 HSCN 4.00 34 HB4O7 9.00 34 H2SeO3 2.6, 8.3, 2.62* 28 Be(OH)2 3.7 4 HSeO3 8.32 77 HBr -9.00 31 H2SeO4 Strong, 2.0 28 HOBr 8.7 28 HSeO4 2.00 34 HOCl 7.53, 7.46 28, 33 H3SiO3 10.0 34 HClO2 2.0 28 H2SO3 1.9, 7.0, 1.76* 28, 77 HClO3 -1.00 28 H2SO4 -3.0, 1.9 28 HClO4 (70%) -10.00 31 HSO3 7.21* 77 CH SO H -0.6 31 3 3 HSO4– 1.99* 77 HCN 9.40 34 H2S2O4 1.9 29 H CO 6.37, 6.35*, 3.58 34, 32 2 3 H2Se
    [Show full text]
  • Thermochemistry of Amino Acids and Constrained Diamines
    W&M ScholarWorks Dissertations, Theses, and Masters Projects Theses, Dissertations, & Master Projects 2012 Thermochemistry of Amino Acids and Constrained Diamines Erica Jane Tullo College of William & Mary - Arts & Sciences Follow this and additional works at: https://scholarworks.wm.edu/etd Part of the Analytical Chemistry Commons, Biochemistry Commons, and the Physical Chemistry Commons Recommended Citation Tullo, Erica Jane, "Thermochemistry of Amino Acids and Constrained Diamines" (2012). Dissertations, Theses, and Masters Projects. Paper 1539623596. https://dx.doi.org/doi:10.21220/s2-vp4j-1g27 This Dissertation is brought to you for free and open access by the Theses, Dissertations, & Master Projects at W&M ScholarWorks. It has been accepted for inclusion in Dissertations, Theses, and Masters Projects by an authorized administrator of W&M ScholarWorks. For more information, please contact [email protected]. Thermochemistry of Amino Acids and Constrained Diamines Erica Jane Tullo Oxford, Pennsylvania Master of Science, The College of William and Mary, 2006 Bachelor of Science, Washington College, 2000 A Dissertation presented to the Graduate Faculty of the College of William and Mary in Candidacy for the Degree of Doctor of Philosophy Department of Applied Science The College of William and Mary January, 2012 APPROVAL PAGE This Dissertation is submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy Committee Chair Marga t Hamilton Professor John C. Poutsma, Chemistry The College of William and Mary Professor Mark K. Hinders, C~r. Applied Science The College of William and Mary 2JtlUJJ Z1C- Assistant Professor Hannes C. Schniepp, Applied Science The College of William and Mary a~ ~L/b/ Professor David E."k:ranbuehl, cfiemistry The College of William and Mary ABSTRACT PAGE The gas-phase proton affinities of several highly basic amino acids and diamines were determined using the extended kinetic method in an ESI-quadrupole ion trap instrument.
    [Show full text]